Windermere Single Family Homes For Rent - 53 homes

Remarks: Available on AUGUST 1, 2026. Move in and enjoy from day one. Inside exclusive 24-hour guard-gated Reserve at Belmere — one of Windermere's most desirable communities. Thr Estate offers over 4,000 square feet of living space. 6 bedrooms, 4.5 bathrooms, a dedicated home office with French doors, and a generous bonus room that's perfect as a playroom, home theater, or game room, there's space here for everyone — whether you're working from home, raising a family, or hosting guests in style. The gourmet kitchen is the true heart of this home, featuring a gas cooktop, double ovens, granite countertops, a breakfast bar, and a sunny breakfast nook. It flows seamlessly into a warm, inviting family room with a fireplace. The downstairs primary suite is your personal retreat, complete with serene pool views and a spa-inspired bath featuring a jacuzzi tub, walk-in shower, and dual vanities. Upstairs, four additional bedrooms — including a convenient Jack-and-Jill configuration — offer flexibility and privacy for family and guests alike. Step outside to a beautifully appointed outdoor living space with a large paved patio, outside full bathroom, summer kitchen. Take advantage of community amenities: fitness center with water views, two tennis courts & basketball courts, volleyball court, and fishing pier. The Reserve at Belmere delivers peace of mind alongside unmatched prestige. Call leasing agent to schedule private tour. Additional fee : $150 monthly pool care

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Yana Ogor (904-400-4192)

Remarks: Sited in the Preserve at Lakes of Windermere, a gated community, this three-bedroom, two-bathroom home sits in a highly desirable location. This single-story home offers a bright, open-concept floor plan with a formal living room, dinning room, family room, kitchen and breakfast nook. The private master bathroom offers a garden tub, separate glassed shower, dual sinks and large walk-in closet. Great backyard area with covered lanai facing conservation. You will not need a car to get to the community's amenities from this home. Enjoy nightly fireworks from your front porch. Lakes of Windermere is conveniently located in the heart of Windermere and offers great amenities, including swimming pool, picnic area, playgrounds and a beautiful lake gazebo. It is just minutes away from Disney attractions, I-4, Winter Garden Grove Shopping and Restaurant Center, SR 408, Florida Turnpike and much more.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Maria Quintero (407-509-0849)

Remarks: Welcome to your dream home in a beautiful cul-de-sac, nestled in a secure, gated community and zoned for top-rated Windermere schools. This fully remodeled, move-in-ready home offers 5 spacious bedrooms plus a large bonus area on the second floor, complete with a half bath. The upgraded chef’s kitchen boasts all new appliances, perfect for entertaining. Relax in your private resort-style pool, or enjoy the convenience of lawn maintenance, pool service, and pest control—all included in the rent. Plus, you’re just minutes from Disney, major highways, and a variety of shops and restaurants. This is the perfect place to call home!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Sevara Botirova Patel (407-242-9546)

Remarks: FOR RENT | Luxury 5-Bedroom Home with Private In-Law Suite in Windermere Welcome to this beautifully updated 5-bedroom, 4-bathroom residence offering 3,365 square feet of elegant living space in one of Windermere’s most desirable communities. This exceptional two-story home has been thoughtfully upgraded with a brand-new roof, two new HVAC systems, updated flooring, fresh paint, and a renovated chef’s kitchen, creating the perfect blend of luxury, comfort, and functionality. Step through the impressive leaded-glass entry doors into a grand foyer with soaring cathedral ceilings and an inviting open layout. The thoughtfully designed three-way split floor plan features hardwood floors, tray ceilings, crown molding, formal living and dining areas, and abundant natural light throughout. The gourmet kitchen is the heart of the home, showcasing granite countertops and backsplash, stainless steel appliances, a large center island with storage, breakfast bar seating, and ample space for entertaining. The spacious primary suite offers private access to the screened lanai and features a luxurious bathroom with dual vanities, a garden tub, walk-in shower, and oversized walk-in closet. One of the home's most desirable features is the private upstairs In-Law Suite, complete with its own bedroom, full bathroom, living area, and dedicated HVAC system—perfect for guests, multigenerational living, a home office, or private retreat. Additional features include: ? 3-Car Garage ? Indoor Laundry Room with Utility Sink ? Screened Covered Patio ? View Disney Fireworks from Home ? Community Pool, Playground & Dog Park ? Top-Rated Schools Including Windermere Prep Nearby ? Minutes to Winter Garden Village, Disney, 429 Expressway, Butler Chain of Lakes, Shopping, Dining & Entertainment This home offers the ultimate Florida lifestyle with space, privacy, and an unbeatable location. Available for immediate occupancy. Schedule your private showing today and discover why this Windermere home is truly one of a kind.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Patricia Zimath, Llc (321-318-1050)

Remarks: Looking for seclusion? One plus acre waterfront. No HOA. Adorable, clean available June 1st. Bring your boat, RV, pets. Quiet treed drive located near the Town of Windermere. Complete with stainless appliances, washer, dryer. Large screened porch. Tile floors throughout. Decorative fireplace in family room. Room to Breathe!! Check it out today. For Application: https://apply.link/rhwVwSc

Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)

Listing Agent: Judy Black (407-810-1803)

Remarks: Mediterranean style property with five bedrooms, four and a half bathrooms on two floors in gated community. New flooring. One of the bedrooms is on the first floor next to a full bathroom, making it ideal to function as an office or guest suite. The remaining bedrooms are on the second floor with the master bedroom has crown molding and a huge walk-in closet. Fully equipped kitchen with granite countertops, stainless steel appliances, and wait, yes, a gas range! To top it all off, it comes with a washer and dryer. The community has a swimming pool, tennis, basketball, sand volleyball, children's play area and weight room. You really must see this property to fully appreciate it. It is professionally managed, and rent includes lawn care, so this is worry-free living. Hurry and schedule a showing, this won't last, and you won't want to miss out. Please see the attached files.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Charles Woolley (407-733-8665)

Remarks: GOLF FRONT!! Beautiful 4-Bed, 3-Bath Home for Rent in the Exclusive Keene’s Pointe Golf Community Nestled in the sought-after and secure gated community of Keene’s Pointe, this stunning single-story home offers a rare opportunity to live in a neighborhood renowned for its strong sense of community and premium amenities. Community Features: • Gated with 24/7 Manned Security: Peace of mind and privacy. • Convenient Amenities: Enjoy access to an on-site restaurant, fitness center, tennis courts, and more—all just a short distance from your doorstep. Property Highlights: • Prime Location: Backing onto the driving range, enjoy serene views of practicing golfers without worrying about stray golf balls. Evenings are quiet and peaceful. • Backyard Oasis: The screened-in pool and spa, complete with heating, create a perfect space for relaxation. A fully equipped summer kitchen adds to the charm for outdoor entertaining. • Spacious Layout: Inside, the home features 4 generously sized bedrooms and a well-designed kitchen with top-of-the-line GE appliances. • Freshly Painted: The interior was recently refreshed in December, offering a clean and inviting atmosphere. • All solid f looring throughout. IAmple Garage Space: A 3-car garage includes a dedicated space for your golf cart. Added Value: • Yard maintenance, pool service, and pest control are included in the rental, providing a relaxed lifestyle. Don’t miss this incredible opportunity to call Keene’s Pointe your home.

Listing is courtesy of: WINDERMERE INTERNATIONAL REALTY (407-421-6241)

Listing Agent: Hans Welbergen (407-701-6814)

Remarks: RECENTLY RENOVATED within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and living room with a gas fireplace. Enjoy the outside grill area and large fenced-in yard. The home has an oversize 2 car garage with a golf cart entrance for those golf enthusiasts.

Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)

Listing Agent: Michelle Corbin (407-491-2690)

Remarks: WATER & ELECTRIC INCLUDED!! MOVE IN JUNE!! Welcome home! 3X2.5 bath 2 story main house 2000 sq ft!! Spacious living area! Perfect for entertaining as it opens to the amazing kitchen that featuring elegant 42" cabinets with beautiful Corian countertops. Elegant French doors in the living room lead to the beautiful view of the courtyard in back. All bedrooms are on the 2nd floor! Primary suite has inviting garden tub, walk-in shower, and an enormous walk-in closet as well as separate vanities!! washer/dryer hookups in utility room as well. A/C, water heater and washer & dryer are new. Resort-style amenities such as exercise room, clubhouse, pool, tennis courts, basketball courts, volleyball/beach area, and a tranquil dock area with amazing views. Easy access to shopping, dinning, and major highways!! Within an approximate 15 min drive to Disney parks! Water and electricity included! Lawn care HOA responsibility. -Garage apartment is rented separately and not included as part of the rental of main house.- -Water & electricity shared by main house and garage apartment. In the event total power & water exceeds $500.00 on any particular month, each tenant/unit will pay overage proportionally based on the average of # of occupants & square footage under AC.- (1x1 garage apartment rented separately but owner will consider renting all on one lease with main house if you are interested (rental price to include main house and 1x1 garage apartment would be negotiated) - 1x1 apartment above garage offers - 380 sq ft of living space under AC with private entrance. Wonderful full kitchen, full bath, spacious living area, and 1 private bedroom- ideal for guests, extended family, office space etc. )

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Joanne Bracero (407-399-8469)

Remarks: Welcome to Waterstone Windermere, with tranquil living and charm, this area boasts connecting lakes, ideal for boating and walking. this property consist of 5 bedrooms, 5 full bathrooms and 2 half baths. it’s 10-15 mins drive from Disney many restaurants and bars, Reputable schools and many other features.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-299-3000)

Listing Agent: Kimroy Mussington (407-299-3000)

Remarks: 3-bedroom, 2.5-bath single family pool home in Lakes of Windermere community. Spacious layout with separate living, dining, and bonus room. The kitchen features a breakfast bar, which is open to the formal dining and dinette areas that overlook the pool/patio. Pool deck/patio is fully screened, and pool service is included. Washer/Dryer are located in the interior laundry room, leading to a two-car garage. There is a total of 2,790 square feet, and 2,229 square feet under air. Community amenities include a pool, picnic area, tennis court, and playground. All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.

Listing is courtesy of: WILSON MANAGEMENT GROUP (407-896-1200)

Listing Agent: Lionel Hebert (407-641-0975)

Remarks: Located in the gated community of Casa Del Lago in Windermere, featuring just 88 luxury homes surrounding Lake Burden, this neighborhood offers an exceptional setting near top-rated schools and only minutes from Orlando’s most popular destinations, including major highways, airports, shopping, dining, and world-renowned attractions. Built by one of the nation’s top private homebuilders, David Weekley Homes, this nearly 4,000-square-foot residence is thoughtfully designed for both everyday living and entertaining. The home features four bedrooms on the first floor, including two bedrooms positioned on the same side of the home that are connected by a shared playroom or bonus space, while each bedroom maintains its own private en suite bathroom. A formal dining room, dedicated private office, and spacious family room provide multiple areas for gathering and daily living. A convenient pool bath is located just off the main living area with direct access to the pool patio. Upstairs, a large loft-style game room offers flexible living space along with a private fifth bedroom featuring its own full bathroom, making it ideal for guests or multigenerational living. Outdoor living is equally impressive with a luxurious paver patio, screened-in pool, and low-maintenance turf backyard, creating a private retreat perfect for year-round Florida living. The home is also fully wired with a comprehensive CCTV security system featuring 21 cameras for added security and peace of mind. Residents also enjoy the prestigious opportunity to become members of the Golden Bear Club, featuring a full-service golf course and clubhouse located in the neighboring community of Keene’s Pointe. Homes in Casa Del Lago rarely come to market, making this a unique opportunity to live in one of Windermere’s most exclusive gated communities.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Matt Kester (772-494-8550)

Remarks: Fully Furnished Executive Rental in downtown Windermere! Welcome to Sunrise on the Lake, a beautifully renovated, fully furnished executive home on Lake Bessie in Windermere. Tucked along winding lakeside roads, this peaceful retreat is perfectly positioned for stunning sunrises, refreshing lake breezes, and panoramic water views. From the moment you arrive, you will appreciate the exceptional curb appeal and expansive front deck overlooking the lake. Chicago brick pavers lead to a mostly single-level, open-concept layout designed for comfort and entertaining. The European inspired living space features a bright dining area with large picture windows and a welcoming family room with premium amenities, including a Sony flat-screen TV, Bose soundbar, electric fireplace, stand-up arcade with 100+ games, foosball table, plus board games and books. The fully equipped kitchen offers stainless steel appliances, remarkable lake views, and opens to the dining area with comfortable seating for eight. Bedrooms provide relaxing, private spaces with views of the home’s half-acre setting. Outside, enjoy a private moon garden with orchids, a shaded dining area beneath a grand oak tree, and a spacious deck perfect for soaking up the Florida sun and enjoying the calm water. The home has recently undergone a complete remodel, with new or newer furnishings throughout, including updated appliances.

Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)

Listing Agent: Simon Simaan (407-558-1396)

Remarks: PLENTY OF SPACE in this beautiful 5-bedroom/4-bath with fully fenced backyard located in desirable Windermere Trails. The home has tile and luxury vinyl throughout (NO CARPET) with plenty of room for families or individuals. Large open floor plan; kitchen with granite countertops, stainless appliances and walk-in pantry; as well as downstairs guest bedroom with ensuite/Jack & Jill bathroom. The master bedroom with large ensuite is on the second floor along with 3 other bedrooms, 2 full bathrooms, laundry room and spacious bonus room. Community includes large pool, playground, cabanas, greenspace and fitness parks, walking trails and dock access. Conveniently located close to highly-rated schools, shopping and restaurants including Lakeside Village Center, Westside Shoppes and Winter Garden Village, as well as Disney, FL-429, FL-408, and I-4. -- No short-term, AirBnB or roommates. Renter’s insurance required.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Carolyn Hunt (407-257-0937)

Remarks: Keene's Pointe gated/24-hour attended home featuring 4 bedrooms, 4 full/2 half baths, formal living and dining rooms, loft, and bonus/game room. This spacious home has low maintenance laminate flooring throughout. The master suite is on the first floor with access to the lanai, walk-in closet with customized shelving and bath with tub, shower and two vanities. The kitchen and family room are centered in the home with multiple doors to the lanai. The family room has a two-story ceiling with gas fireplace and built-ins. Upstairs you will find a loft with built-in cabinetry that can also be a study, bonus/game room over the garage with full bath and three additional bedrooms (one is an en-suite and the other two share a hall bath). The back yard is spacious and has a large pool/spa with fencing and covered lanai. There is also a three car garage large enough to house a golf cart. Shallow well for irrigation, newer roof and gutters are just some of the great features of this home.

Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)

Listing Agent: Teresa Stewart (407-493-3057)

Remarks: Stunning Beautiful Upgraded home in the desirable Wickham Park community in heart of Windermere. NO carpet. Perfect location. Top rated schools. Rent includes hoa fee and lawncare. Well-maintained 4 bedroom & 2.5 bath & 1 loft/retreat upstairs & 2 car garage on front. Sizable back yard with extended pave. Open floor plan with lots of upgrades. Great natural light in the whole house. Master bedroom downstairs with upgraded bath tub, shower, vanity, lighting fixtures and walk-in closet. Upstairs there are 3 bedrooms and 1 loft area for multiple game/retreat/study/open office. Community amenities includess clubhouse pool, walking/biking trails, dog park, playground. Perfectly convenient for the grocery shoppings, restaurants, schools, entertainment, daily living essentials. Closed to Disney World. Short drive to downtown of Orlando, Winter Garden. Schedule a showing today!

Listing is courtesy of: YORK MILLS REALTY LLC (626-328-8535)

Listing Agent: Jacky Liu (407-921-5670)

Remarks: Located in the highly sought-after Summerport community in Windermere, this move-in ready home offers the perfect combination of location, comfort, and everyday convenience. Zoned for highly rated schools and just minutes from Horizon West, Disney, downtown Winter Garden, shopping, dining, and major roadways including SR-429 and the Florida Turnpike, the location is hard to beat. Inside, you’ll find a spacious and functional floor plan featuring brand-new carpet, fresh interior and exterior paint, granite countertops, wood cabinetry, a gas range, gas water heater, and abundant natural light throughout. The flexible bonus room is ideal for a home office, playroom, gym, or additional living space. The primary suite features a walk-in closet and private en-suite bathroom designed for comfort and privacy. A new washer and dryer are also included, making this home truly move-in ready. Step outside to a screened-in patio overlooking a peaceful pond view, creating the perfect setting for morning coffee or relaxing evenings with no rear neighbors directly behind you. The front yard landscaping and charming curb appeal further enhance the home’s welcoming feel. Residents of Summerport enjoy access to resort-style amenities including a community pool, fitness center, tennis courts, parks, playgrounds, sidewalks, walking trails, and scenic lakes throughout the neighborhood. With its ideal location, recent updates, and desirable community amenities, this home is an excellent opportunity in one of Windermere’s most popular communities.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Evan Caulfield (407-432-9767)

Remarks: Luxury one-level Mediterranean Style home located in the highly desirable Enclave community at WINDERMERE. This elegant home is Energy Star Certified and also come with Solar Panels, monthly electric bill is only around $33! Step into the grand entryway with extensive natural light throughout, this 4 bedrooms, 2 baths with an office home deliver a bright open atmosphere. Open floor open, well maintained with ceramic tile on living area and laminate floor on all bedrooms. The master bedroom, the living room and the eating area overlook the tranquil pond at the back, not only creating a beautiful water view, but also providing a peaceful backdrop and exceptional Privacy. Relax in the screened patio or the back yard to enjoy the peaceful water scenery. The chef inspired gourmet kitchen features granite countertops, 42" cabinetry and SS Appliances. The Master Bedroom features elegant tray ceiling. Master bathroom has a garden tub, spacious shower, dual vanities and a large walk-in Closet. All bedrooms have walk-in closets with custom built-in shelving. Great school district! Just a few minutes to Windermere High School and Windermere Preparatory School. Walking distance to Sunset Park Elementary. Enclave is a beautiful community features all roof tile luxury houses. It is located on Chase Road next to Keene’s Point and Gold Bear Golf and Country Club. Easy access to SR 429, Turnpike and 408. Close to Disney Theme Parks. Shopping, dining and attractions are all within a vibrant area. Windermere ranked number one as the best place to live for suburbanites in Florida. Must see! Call now to schedule a showing!

Listing is courtesy of: SUNSHINE REALTY & PROP. MGNT (407-341-8754)

Listing Agent: Man Ching Wong (407-341-8754)

Remarks: Discover refined Florida living in this stunning 5-bedroom, 3.5-bathroom home located in the sought-after Ashlei Park community in Windermere. Designed with both elegance and functionality in mind, this spacious residence offers an exceptional layout ideal for comfortable family living and entertaining. Step inside to find bright, open living spaces filled with natural light, complemented by stylish finishes and generous room sizes throughout. The gourmet kitchen seamlessly connects to the main living areas, creating the perfect setting for everyday living and hosting guests. The beautifully landscaped backyard provides a private retreat where you can relax and enjoy the Florida lifestyle year-round. The outdoor patio is ideal for barbecues, gatherings, and peaceful evenings outdoors. Additional features include a two-car garage and abundant storage space throughout the home. Conveniently located in the highly desirable Windermere area, residents enjoy easy access to top-rated schools, premier shopping, dining, entertainment, and major attractions throughout Central Florida. This exceptional Ashlei Park home offers the perfect combination of luxury, comfort, and convenience. Schedule your private showing today and experience everything this beautiful rental property has to offer!

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Simone Pinto De Almeida Santos (407-371-2893)

Remarks: 5 bedroom, 3 bath home nestled in the community of Windermere Sound. Located near schools, parks, shopping and more, this home is waiting for you! A Large house like this, is sure not to last long.

Listing is courtesy of: BLUEHOUSE REALTY GROUP LLC (929-391-3985)

Listing Agent: Donny Hang Fung (929-391-3985)